JP6703739B2 - Composition for N-vinyllactam polymerization - Google Patents
Composition for N-vinyllactam polymerization Download PDFInfo
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- JP6703739B2 JP6703739B2 JP2015211431A JP2015211431A JP6703739B2 JP 6703739 B2 JP6703739 B2 JP 6703739B2 JP 2015211431 A JP2015211431 A JP 2015211431A JP 2015211431 A JP2015211431 A JP 2015211431A JP 6703739 B2 JP6703739 B2 JP 6703739B2
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- vinyllactam
- polymerization
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- 238000006116 polymerization reaction Methods 0.000 title claims description 25
- 239000000203 mixture Substances 0.000 title claims description 14
- 239000000178 monomer Substances 0.000 claims description 41
- 229920000642 polymer Polymers 0.000 claims description 28
- 229920002554 vinyl polymer Polymers 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 239000003638 chemical reducing agent Substances 0.000 claims description 9
- 150000001451 organic peroxides Chemical class 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
- -1 N-vinyl-3-methyl-2-pyrrolidone N-vinyl-3-ethyl-2-pyrrolidone Chemical compound 0.000 description 9
- 239000003505 polymerization initiator Substances 0.000 description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 5
- OIXFWERBTHZQQH-UHFFFAOYSA-N 4-hydroperoxy-4-methylpentan-2-ol Chemical compound CC(O)CC(C)(C)OO OIXFWERBTHZQQH-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- WHBWUNCJQHRHKD-UHFFFAOYSA-N 3-hydroperoxy-3-methylbutan-1-ol Chemical compound OOC(C)(C)CCO WHBWUNCJQHRHKD-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- JHYYINIEKJKMDD-UHFFFAOYSA-N 1-ethenyl-3,3-dimethylpyrrolidin-2-one Chemical compound CC1(C)CCN(C=C)C1=O JHYYINIEKJKMDD-UHFFFAOYSA-N 0.000 description 1
- VNKSQJMKZBPKQH-UHFFFAOYSA-N 1-ethenyl-3-propylpyrrolidin-2-one Chemical compound CCCC1CCN(C=C)C1=O VNKSQJMKZBPKQH-UHFFFAOYSA-N 0.000 description 1
- TVAXBMZXTAQVPS-UHFFFAOYSA-N 1-ethenyl-4-ethylpyrrolidin-2-one Chemical compound CCC1CN(C=C)C(=O)C1 TVAXBMZXTAQVPS-UHFFFAOYSA-N 0.000 description 1
- BFQIRRXYIIKQBX-UHFFFAOYSA-N 1-ethenyl-4-methyl-5-propylpyrrolidin-2-one Chemical compound CCCC1C(C)CC(=O)N1C=C BFQIRRXYIIKQBX-UHFFFAOYSA-N 0.000 description 1
- LWWJIQWIJBMGKE-UHFFFAOYSA-N 1-ethenyl-4-methylpyrrolidin-2-one Chemical compound CC1CN(C=C)C(=O)C1 LWWJIQWIJBMGKE-UHFFFAOYSA-N 0.000 description 1
- UFBGFFRWZFQSRM-UHFFFAOYSA-N 1-ethenyl-4-propylpyrrolidin-2-one Chemical compound CCCC1CN(C=C)C(=O)C1 UFBGFFRWZFQSRM-UHFFFAOYSA-N 0.000 description 1
- CKEOJHRBPVOLGO-UHFFFAOYSA-N 1-ethenyl-5-ethyl-4-methylpyrrolidin-2-one Chemical compound CCC1C(C)CC(=O)N1C=C CKEOJHRBPVOLGO-UHFFFAOYSA-N 0.000 description 1
- UUJDYNPZEYGKOF-UHFFFAOYSA-N 1-ethenyl-5-ethyl-5-methylpyrrolidin-2-one Chemical compound CCC1(C)CCC(=O)N1C=C UUJDYNPZEYGKOF-UHFFFAOYSA-N 0.000 description 1
- DJABNVJZYFGAJE-UHFFFAOYSA-N 1-ethenyl-5-ethylpyrrolidin-2-one Chemical compound CCC1CCC(=O)N1C=C DJABNVJZYFGAJE-UHFFFAOYSA-N 0.000 description 1
- NMRXKEKPFLHTNP-UHFFFAOYSA-N 1-ethenyl-5-methylazepan-2-one Chemical compound CC1CCN(C=C)C(=O)CC1 NMRXKEKPFLHTNP-UHFFFAOYSA-N 0.000 description 1
- HQGPZXPTJWUDQR-UHFFFAOYSA-N 1-ethenyl-5-methylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1C=C HQGPZXPTJWUDQR-UHFFFAOYSA-N 0.000 description 1
- PKSFSHKIYPHICB-UHFFFAOYSA-N 1-ethenyl-5-propylpyrrolidin-2-one Chemical compound CCCC1CCC(=O)N1C=C PKSFSHKIYPHICB-UHFFFAOYSA-N 0.000 description 1
- AVLAUYSPRNKPOT-UHFFFAOYSA-N 1-ethenyl-7-methylazepan-2-one Chemical compound CC1CCCCC(=O)N1C=C AVLAUYSPRNKPOT-UHFFFAOYSA-N 0.000 description 1
- ULJZDERCDUYLKS-UHFFFAOYSA-N 1-ethenyl-7-propylazepan-2-one Chemical compound CCCC1CCCCC(=O)N1C=C ULJZDERCDUYLKS-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- QENRKQYUEGJNNZ-UHFFFAOYSA-N 2-methyl-1-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound CC(C)C(S(O)(=O)=O)NC(=O)C=C QENRKQYUEGJNNZ-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- GLLAFCHUFGZONA-UHFFFAOYSA-N 3-butyl-1-ethenylpyrrolidin-2-one Chemical compound CCCCC1CCN(C=C)C1=O GLLAFCHUFGZONA-UHFFFAOYSA-N 0.000 description 1
- LIPHPCKTNVMODD-UHFFFAOYSA-N 4-butyl-1-ethenylpyrrolidin-2-one Chemical compound CCCCC1CN(C=C)C(=O)C1 LIPHPCKTNVMODD-UHFFFAOYSA-N 0.000 description 1
- FDJCPISNCHBARD-UHFFFAOYSA-N 5-butyl-1-ethenylpyrrolidin-2-one Chemical compound CCCCC1CCC(=O)N1C=C FDJCPISNCHBARD-UHFFFAOYSA-N 0.000 description 1
- LXEKPEMOWBOYRF-QDBORUFSSA-N AAPH Chemical compound Cl.Cl.NC(=N)C(C)(C)\N=N\C(C)(C)C(N)=N LXEKPEMOWBOYRF-QDBORUFSSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- 241000047703 Nonion Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000010350 erythorbic acid Nutrition 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 229940026239 isoascorbic acid Drugs 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium erythorbate Chemical compound [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 235000010352 sodium erythorbate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
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- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
本発明は、有機過酸化物を含有するＮ−ビニルラクタム重合用組成物に関する。詳しくは、重合後の残存モノマーが少なく、臭気の少ないポリマーを得ることができ、重合開始剤として使用可能な水酸基含有有機過酸化物を含むＮ−ビニルラクタム重合用組成物に関する。 The present invention relates to a composition for N-vinyllactam polymerization containing an organic peroxide. More specifically, the present invention relates to a composition for N-vinyllactam polymerization containing a hydroxyl group-containing organic peroxide that can be used as a polymerization initiator and that can give a polymer having a small amount of residual monomers after polymerization and a low odor.
Ｎ−ビニルラクタム重合体は、分散剤、増粘剤、接着剤、化粧品、医薬品、賦形剤など多種多様な用途に使用されており、その性能や安全性の向上が求められている。 N-vinyllactam polymers are used in a wide variety of applications such as dispersants, thickeners, adhesives, cosmetics, pharmaceuticals and excipients, and their performance and safety are required to be improved.
これまでに、Ｎ−ビニルラクタム重合体中の残存モノマー低減、重合体の性能および安全性を向上させる方法が開示されている。 Heretofore, methods for reducing residual monomers in N-vinyllactam polymers and improving polymer performance and safety have been disclosed.
特許文献１には、Ｎ−ビニルラクタムの重合において、重合開始剤として過硫酸塩やアゾ系開始剤を使用せず、ハイドロパーオキサイドとロンガリットを併用したレドックス系を用いることで、重合開始剤由来の有毒な分解生成物が生じることなく、重合体の重合度低下を抑制する方法が開示されている。 In Patent Document 1, in the polymerization of N-vinyllactam, by using a redox system in which hydroperoxide and Rongalit are used in combination without using a persulfate or an azo initiator as a polymerization initiator, the polymerization initiator is derived. A method for suppressing a decrease in the degree of polymerization of a polymer without the generation of toxic decomposition products of the above is disclosed.
特許文献２には、Ｎ−ビニルラクタムの重合において、重合開始剤としてt-ブチルハイドロパーオキサイドと亜硫酸塩を併用したレドックス系を用いることで、ポリマー水溶液の着色および臭気が少なく、不純物が極めて少ない重合体が得られる方法が開示されている。 In Patent Document 2, in the polymerization of N-vinyllactam, by using a redox system in which t-butyl hydroperoxide and a sulfite are used in combination as a polymerization initiator, coloring and odor of an aqueous polymer solution are small and impurities are extremely small. A method of obtaining a polymer is disclosed.
特許文献１と特許文献２に記載されている、重合開始剤の併用系を用いて得られたＮ−ビニルラクタム重合体は、還元剤であるロンガリットから副生するホルムアルデヒドが環境や人体への影響を与える可能性があることや、残存モノマー量の低減が未だ十分であることから、その改善が望まれている。 The N-vinyllactam polymer obtained by using the combination system of the polymerization initiators described in Patent Document 1 and Patent Document 2 has an effect on the environment and human body by formaldehyde produced as a by-product from Rongalit which is a reducing agent. Therefore, there is a need for improvement of the amount of residual monomers, because the reduction of residual monomer amount is still sufficient.
本発明は、残存モノマー量が少なく、かつ臭気が少ないＮ−ビニルラクタム重合体を得ることができる、Ｎ−ビニルラクタム重合用組成物を提供するものである。 The present invention provides a composition for N-vinyllactam polymerization capable of obtaining an N-vinyllactam polymer having a small amount of residual monomers and a low odor.
すなわち本発明は、下記のものである。
［１］（Ａ）Ｎ−ビニルラクタムを含むビニルモノマー組成物；１００質量部、
（Ｂ）一般式（Ｉ）で表される水酸基含有有機過酸化物；０．１００〜２質量部、
[式中Ｒは水素原子またはメチル基]
（Ｃ）還元剤；０．００５〜２質量部、および、
（Ｄ）水；１００〜１０００質量部、
を含むＮ−ビニルラクタム重合用組成物を水溶液重合に供することによって、Ｎ−ビニルラクタム重合体を得ることを特徴とする、Ｎ−ビニルラクタム重合体の製造方法。
Thus, the present invention follows.
[1] (A) Vinyl monomer composition containing N-vinyl lactam; 100 parts by mass,
(B) Hydroxyl group-containing organic peroxide represented by the general formula (I); 0.100 to 2 parts by mass,
[Wherein R is a hydrogen atom or a methyl group]
(C) reducing agent; 0.005 to 2 parts by mass, and
(D) water; 100 to 1000 parts by mass,
A method for producing an N-vinyllactam polymer, characterized in that an N-vinyllactam polymer is obtained by subjecting an N-vinyllactam polymerization composition containing the above to aqueous solution polymerization .
本発明の組成物によれば、特定の水酸基含有有機過酸化物をＮ−ビニルラクタム重合用組成物の重合開始剤に使用することにより、残存モノマーが少ないＮ−ビニルラクタム重合体を得ることができる。 According to the composition of the present invention, by using a specific hydroxyl group-containing organic peroxide as a polymerization initiator of a composition for N-vinyllactam polymerization, an N-vinyllactam polymer having a small amount of residual monomers can be obtained. it can.
本発明において、Ｎ−ビニルラクタム重合体とは、ポリビニルラクタム（単独重合体）およびＮ−ビニルラクタムを構成単位として含む共重合体を意味する。 In the present invention, the N-vinyllactam polymer means a polyvinyllactam (homopolymer) and a copolymer containing N-vinyllactam as a constituent unit.
本発明のＮ−ビニルラクタム重合用組成物は、（Ａ）Ｎ−ビニルラクタムを含むビニルモノマー組成物、（Ｂ）水酸基含有有機過酸化物、（Ｃ）還元剤および（Ｄ）水を含む組成物である。 The composition for N-vinyllactam polymerization of the present invention comprises (A) a vinyl monomer composition containing N-vinyllactam, (B) a hydroxyl group-containing organic peroxide, (C) a reducing agent, and (D) water. It is a thing.
本発明に用いられる、Ｎ−ビニルラクタムとその他ビニルモノマーとの割合は任意であるが、水溶性モノマーが好ましい。 The ratio of N-vinyllactam to other vinyl monomers used in the present invention is arbitrary, but water-soluble monomers are preferred.
本発明において、用いることができるＮ−ビニルラクタムとしては、Ｎ−ビニル−２−ピロリドン、Ｎ−ビニル−３−メチル−２−ピロリドンＮ−ビニル−３−エチル−２−ピロリドン、Ｎ−ビニル−３−プロピル−２−ピロリドン、Ｎ−ビニル−３−ブチル−２−ピロリドン、Ｎ−ビニル−３，３−ジメチル−２−ピロリドン、Ｎ−ビニル−４−メチル−２−ピロリドン、Ｎ−ビニル−４−エチル−２−ピロリドン、Ｎ−ビニル−４−プロピル−２−ピロリドン、Ｎ−ビニル−４−ブチル−２−ピロリドン、Ｎ−ビニル−５−メチル−２−ピロリドン、Ｎ−ビニル−５−エチル−２−ピロリドン、Ｎ−ビニル−５−プロピル−２−ビロリドン、Ｎ−ビニル−５−ブチル−２−ピロリドン、Ｎ−ビニル−４−メチル−５−プロピルピロリドン、Ｎ−ビニル−４−メチル−５−エチルピロリドン、Ｎ−ビニル−５−メチル−５−エチルピロリドン、Ｎ−ビニルカプロラクタム、Ｎ−ビニル−４−メチルカプロラクタム、Ｎ−ビニル−６−メチルカプロラクタム、Ｎ−ビニル−６−プロピルカプロラクタム、Ｎ−ビニル−７−ブチルカプロラクタム、Ｎ−ビニル−２−ピペリドン等が挙げられる。 In the present invention, as N-vinyllactam that can be used, N-vinyl-2-pyrrolidone, N-vinyl-3-methyl-2-pyrrolidone N-vinyl-3-ethyl-2-pyrrolidone, N-vinyl- 3-propyl-2-pyrrolidone, N-vinyl-3-butyl-2-pyrrolidone, N-vinyl-3,3-dimethyl-2-pyrrolidone, N-vinyl-4-methyl-2-pyrrolidone, N-vinyl- 4-ethyl-2-pyrrolidone, N-vinyl-4-propyl-2-pyrrolidone, N-vinyl-4-butyl-2-pyrrolidone, N-vinyl-5-methyl-2-pyrrolidone, N-vinyl-5- Ethyl-2-pyrrolidone, N-vinyl-5-propyl-2-pyrrolidone, N-vinyl-5-butyl-2-pyrrolidone, N-vinyl-4-methyl-5-propylpyrrolidone, N-vinyl-4-methyl -5-ethylpyrrolidone, N-vinyl-5-methyl-5-ethylpyrrolidone, N-vinylcaprolactam, N-vinyl-4-methylcaprolactam, N-vinyl-6-methylcaprolactam, N-vinyl-6-propylcaprolactam , N-vinyl-7-butylcaprolactam, N-vinyl-2-piperidone and the like.
本発明において、Ｎ−ビニルラクタム系重合体は、その一部にＮ−ビニルラクタム以外のモノマーを含んでもよく、用いることのできるモノマーとしては、カルボン酸基含有モノマー、スルホン酸基含有モノマー、ノニオン性親水基含有モノマー、メチロール基含有モノマー、Ｎ−ビニル系モノマー、アミノ基含有不飽和モノマー、およびアクリル酸エステル等が挙げられる。詳しくは、カルボン酸基含有モノマーとしては、アクリル酸、メタクリル酸、イタコン酸、マレイン酸、フマル酸、クロトン酸、およびソルビン酸等；スルホン酸基含有モノマーとしては、２−（メタ）アクリロイルエタンスルホン酸、２−（メタ）アクリロイルプロパンスルホン酸、２−（メタ）アクリルアミド−２−メチルプロパンスルホン酸、ビニルスルホン酸、およびスチレンスルホン酸等、およびそれらの塩；ノニオン性親水基含有モノマーとしては、メタクリルアミド、Ｎ−置換（メタ）アクリルアミド、２−ヒドロキシエチル（メタ）アクリレート、２−ヒドロキシプロピル（メタ）アクリレート、メトキシポリエチレングリコール（メタ）アクリレート、およびポリエチレングリコール（メタ）アクリレート等；Ｎ−ビニル基含有モノマーとしては、Ｎ−ビニルアセトアミド、Ｎ−ビニルホルムアミド、Ｎ−ビニルカルバゾール等；メチロール基含有モノマーとしては、Ｎ−メチロールアクリルアミド等；アミノ基含有不飽和モノマーとしては、Ｎ，Ｎ−ジメチルアミノエチル（メタ）アクリレート、Ｎ，Ｎ−ジメチルアミノプロピル（メタ）アクリレート、およびＮ，Ｎ−ジメチルアミノプロピル（メタ）アクリルアミド等、およびそれらの４級アンモニウム塩；アクリル酸エステルとしては、メチル（メタ）アクリレート、およびエチル（メタ）アクリレート等が挙げられる。 In the present invention, the N-vinyl lactam polymer may include a monomer other than N-vinyl lactam in a part thereof, and usable monomers include a carboxylic acid group-containing monomer, a sulfonic acid group-containing monomer, and a nonion. Examples of the hydrophilic hydrophilic group-containing monomer, methylol group-containing monomer, N-vinyl-based monomer, amino group-containing unsaturated monomer, acrylic acid ester, and the like. Specifically, the carboxylic acid group-containing monomer is acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, crotonic acid, sorbic acid, etc.; The sulfonic acid group-containing monomer is 2-(meth)acryloylethane sulfone. Acid, 2-(meth)acryloyl propane sulfonic acid, 2-(meth)acrylamido-2-methyl propane sulfonic acid, vinyl sulfonic acid, styrene sulfonic acid and the like, and salts thereof; as the nonionic hydrophilic group-containing monomer, Methacrylamide, N-substituted (meth)acrylamide, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, polyethylene glycol (meth)acrylate, etc.; N-vinyl group Examples of the contained monomer are N-vinylacetamide, N-vinylformamide, N-vinylcarbazole, etc.; As the methylol group-containing monomer, N-methylolacrylamide etc.; As the amino group-containing unsaturated monomer, N,N-dimethylaminoethyl (Meth)acrylate, N,N-dimethylaminopropyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylamide and the like, and quaternary ammonium salts thereof; as acrylic acid ester, methyl (meth)acrylate , And ethyl (meth)acrylate.
本発明においてＮ−ビニルラクタム系重合体は、任意で架橋させてもよく、架橋させる場合は、架橋性のモノマーを用いることができる。架橋性のモノマーとしては、ジビニルベンゼン、Ｎ，Ｎ′−メチレンビス（メタ）アクリルアミド、（ポリ）エチレングリコールジ（メタ）アクリレート、グリセリントリ（メタ）アクリレート、およびトリメチロールプロパントリ（メタ）アクリレート等が挙げられる。さらにこれらの２種以上を選択して用いることもできる。 In the present invention, the N-vinyl lactam polymer may be optionally crosslinked, and in the case of crosslinking, a crosslinkable monomer can be used. Examples of the crosslinkable monomer include divinylbenzene, N,N′-methylenebis(meth)acrylamide, (poly)ethylene glycol di(meth)acrylate, glycerin tri(meth)acrylate, and trimethylolpropane tri(meth)acrylate. Can be mentioned. Furthermore, two or more of these may be selected and used.
本発明で用いる水酸基含有有機過酸化物としては、３−ヒドロキシ−１，１−ジメチルブチルヒドロペルオキシド（式１のＲ＝メチル基）および３−ヒドロキシ−１，１−ジメチルプロピルヒドロペルオキシド（式１のＲ＝水素原子）が挙げられる。 Examples of the hydroxyl group-containing organic peroxide used in the present invention include 3-hydroxy-1,1-dimethylbutyl hydroperoxide (R=methyl group of Formula 1) and 3-hydroxy-1,1-dimethylpropyl hydroperoxide (Formula 1). R = hydrogen atom).
３−ヒドロキシ−１，１−ジメチルブチルヒドロペルオキシドおよび３−ヒドロキシ−１，１−ジメチルプロピルヒドロペルオキシドは単独で使用されても良いし、併用されても良い。 3-hydroxy-1,1-dimethylbutyl hydroperoxide and 3-hydroxy-1,1-dimethylpropyl hydroperoxide may be used alone or in combination.
本発明において、水酸基含有有機過酸化物は、（Ａ）Ｎ−ビニルラクタムを含むビニルモノマー組成物１００質量部に対して、０．００５〜２質量部を用いる。好ましくは、０．０１〜１質量部である。また、重合反応の後期に残存モノマー低減のために追加することも可能である。 In the present invention, the hydroxyl group-containing organic peroxide is used in an amount of 0.005 to 2 parts by mass with respect to 100 parts by mass of the vinyl monomer composition containing (A) N-vinyllactam. It is preferably 0.01 to 1 part by mass. It is also possible to add it in the latter stage of the polymerization reaction in order to reduce the residual monomer.
本発明において、水酸基含有有機過酸化物は、還元剤を併用することでレドックス反応を起こして活性ラジカルを生じ、生じた活性ラジカルによりＮ−ビニルラクタムを含むビニルモノマーの重合が開始し、Ｎ−ビニルラクタム重合体が生成する。 In the present invention, the hydroxyl group-containing organic peroxide is used in combination with a reducing agent to cause a redox reaction to generate an active radical, and the generated active radical initiates the polymerization of the vinyl monomer containing N-vinyllactam, A vinyl lactam polymer is formed.
本発明で用いる還元剤としては、アスコルビン酸、イソアスコルビン酸、イソアスコルビン酸ナトリウム、酒石酸、ロンガリット、糖類、ホルマリン、硫酸第一鉄、硫酸銅、亜硫酸ナトリウム、重亜硫酸ナトリウム、およびチオ尿素等を用いることができる。 As the reducing agent used in the present invention, ascorbic acid, isoascorbic acid, sodium isoascorbate, tartaric acid, rongalite, saccharides, formalin, ferrous sulfate, copper sulfate, sodium sulfite, sodium bisulfite, and thiourea are used. be able to.
本発明において還元剤は、Ｎ−ビニルラクタムを含むビニルモノマーの総量１００質量部に対して、０．００５〜２質量部を用いる。好ましくは、０．０１〜１質量部である。 In the present invention, the reducing agent is used in an amount of 0.005 to 2 parts by mass based on 100 parts by mass of the total amount of vinyl monomers containing N-vinyllactam. It is preferably 0.01 to 1 part by mass.
本発明において、水は水溶液重合における溶媒であるために必須の構成成分であり、Ｎ−ビニルラクタムを含むビニルモノマーの総量１００質量部に対して、１００〜１０００質量部を用いる。 In the present invention, water is an essential constituent component because it is a solvent in aqueous solution polymerization, and 100 to 1000 parts by mass is used for 100 parts by mass of the total amount of vinyl monomers including N-vinyllactam.
本発明のＮ−ビニルラクタム重合体には、必要に応じて公知の添加剤を加えることもできる。添加剤としては、可塑剤、無機もしくは有機充填剤、増粘剤、および有機溶剤等が挙げられる。 Known additives may be added to the N-vinyllactam polymer of the present invention, if necessary. Examples of the additive include a plasticizer, an inorganic or organic filler, a thickener, and an organic solvent.
本発明のＮ−ビニルラクタムを含むビニルモノマー組成物の重合は、水溶液重合法とする。製造方式（バッチもしくは連続）、重合温度、攪拌の有無、加圧の有無、連鎖移動剤の有無、重合停止剤の有無を任意に選択することで、分子量、ゲル含有量、分子末端構造を制御することが可能である。 The polymerization of the vinyl monomer composition containing N-vinyllactam of the present invention is an aqueous solution polymerization method . Controlling the molecular weight, gel content, and molecular end structure by arbitrarily selecting the manufacturing method (batch or continuous), polymerization temperature, presence of stirring, presence of pressure, presence of chain transfer agent, presence of polymerization terminator It is possible to
Ｎ−ビニルラクタム重合体の水溶液重合においては、公知の水溶液重合法を用いることができ、モノマーおよびその他のメルカプタン類等の連鎖移動剤、各種消泡剤等を初期に一括、または連続して添加してもよいし、その一部を重合中に連続、または分割して添加してもよい。 In the aqueous solution polymerization of the N-vinyllactam polymer, a known aqueous solution polymerization method can be used, and a chain transfer agent such as a monomer and other mercaptans, various defoaming agents, etc. are initially added all at once or continuously. Alternatively, a part thereof may be added continuously or divided during the polymerization.
Ｎ−ビニルラクタム重合体の精製方法、回収方法、乾燥方法、および細断方法は、公知技術を適用することができる。 Known techniques can be applied to the method for purifying, recovering, drying, and shredding the N-vinyllactam polymer.
以下、本発明を実施例に基づき説明するが、本発明はこれらの実施例に限定されるものではない。なお、実施例および比較例中に記載される「部」は、全て質量基準である。 Hereinafter, the present invention will be described based on examples, but the present invention is not limited to these examples. In addition, all "parts" described in Examples and Comparative Examples are based on mass.
＜Ｎ−ビニル−２−ピロリドン重合体の製造＞ <Production of N-vinyl-2-pyrrolidone polymer>
（実施例１）
フラスコに水２００部および１％亜硫酸ナトリウム水溶液１０部を加えた後、窒素置換を行いながら８０℃まで昇温した。攪拌しながら、Ｎ−ビニル−２−ピロリドン１００部と、１％３−ヒドロキシ−１，１−ジメチルブチルヒドロペルオキシド水溶液１０部を３時間かけて滴下した。滴下終了後、さらに３時間重合を行い、重合体を得た。
(Example 1)
After adding 200 parts of water and 10 parts of a 1% sodium sulfite aqueous solution to the flask, the temperature was raised to 80° C. while performing nitrogen substitution. With stirring, 100 parts of N-vinyl-2-pyrrolidone and 10 parts of a 1% 3-hydroxy-1,1-dimethylbutyl hydroperoxide aqueous solution were added dropwise over 3 hours. After the dropping was completed, the polymerization was further performed for 3 hours to obtain a polymer.
（実施例２〜５）
重合に使用したモノマー、重合開始剤、還元剤および水を下記表１に記載する種類及び配合量に変更した以外は、実施例１−１と同様にして重合を行い、重合体を得た。
(Examples 2 to 5)
Polymerization was carried out in the same manner as in Example 1-1, except that the types and blending amounts shown in Table 1 below were used for the monomers, polymerization initiators, reducing agents and water used for the polymerization, to obtain a polymer.
（比較例１）
フラスコに水２００部および１％亜硫酸ナトリウム水溶液１０部を加えた後、窒素置換を行いながら８０℃まで昇温した。攪拌しながら、Ｎ−ビニル−２−ピロリドン１００部と、１％t-ブチルヒドロペルオキシド水溶液１０部を３時間かけて滴下した。滴下終了後、さらに３時間重合を行い、重合体を得た。
(Comparative Example 1)
After adding 200 parts of water and 10 parts of a 1% sodium sulfite aqueous solution to the flask, the temperature was raised to 80° C. while performing nitrogen substitution. With stirring, 100 parts of N-vinyl-2-pyrrolidone and 10 parts of a 1% t-butyl hydroperoxide aqueous solution were added dropwise over 3 hours. After the dropping was completed, the polymerization was further performed for 3 hours to obtain a polymer.
（比較例２、３）
重合に使用した重合開始剤および還元剤を下記表１に記載する種類及び配合量に変更した以外は、比較例１と同様にして重合を行い、重合体を得た。
(Comparative examples 2 and 3)
Polymerization was carried out in the same manner as in Comparative Example 1 except that the types and blending amounts shown in Table 1 below were used for the polymerization initiator and the reducing agent used for the polymerization to obtain a polymer.
＜評価方法＞
各実施例及び比較例で得られた溶液を、下記試験法によって評価した。得られた評価結果を下記表１に示す。
<Evaluation method>
The solutions obtained in the respective examples and comparative examples were evaluated by the following test methods. The evaluation results obtained are shown in Table 1 below.
（残存モノマー量の測定）
液体クロマトグラフィーを用いて、得られたＮ−ビニルラクタム重合体中に残存するモノマーの含有量を測定した。残存モノマー量を以下基準に分類し、判定した。
評価基準：○…残存モノマー量が１００ｐｐｍ未満
△…残存モノマー量が１００ｐｐｍ以上、５００ｐｐｍ未満
×…残存モノマー量が５００ｐｐｍ以上
(Measurement of residual monomer amount)
The content of the residual monomer in the obtained N-vinyllactam polymer was measured by liquid chromatography. The amount of residual monomer was classified according to the following criteria and judged.
Evaluation criteria: ◯... residual monomer amount is less than 100 ppm
Δ: The residual monomer amount is 100 ppm or more and less than 500 ppm
×: The residual monomer amount is 500 ppm or more
（臭気）
重合直後のポリマー水溶液の臭気を下記の基準で判定した。
○・・・ほとんど臭気のないもの
△・・・わずかに臭気があるもの
×・・・臭気があるもの
(Odor)
The odor of the polymer aqueous solution immediately after the polymerization was judged according to the following criteria.
○: Almost no odor △: Slight odor ×: Odor
ＮＶＰＲ：Ｎ−ビニル−２−ピロリドン
ＮＶＰＰ：Ｎ−ビニルピペリドン
ＡＡｍ：アクリルアミド
ＤＨＢ−ＨＰＯ：３−ヒドロキシ−１，１−ジメチルブチルヒドロペルオキシド
ＤＨＰ−ＨＰＯ：３−ヒドロキシ−１，１−ジメチルプロピルヒドロペルオキシド
ＴＢ−ＨＰＯ：t-ブチルヒドロペルオキシド
Ｃ−ＨＰＯ：クミルヒドロペルオキシド
ＡＡＰＨ：２，２−アゾビス−２−アミジノプロパンジヒドロクロリド
ＳＳ：亜硫酸ナトリウム（Sodium Sulfite）
ＡＡ：アスコルビン酸（Ascorbic Acid）
ＳＦＳ：ロンガリット（Sodium Formaldehyde Sulfoxylate）
NVPR: N-vinyl-2-pyrrolidone
NVPP: N-Vinylpiperidone
AAm: Acrylamide DHB-HPO: 3-Hydroxy-1,1-dimethylbutylhydroperoxide DHP-HPO: 3-Hydroxy-1,1-dimethylpropylhydroperoxide TB-HPO: t-Butylhydroperoxide C-HPO: Cumyl Hydroperoxide
AAPH: 2,2-azobis-2-amidinopropane dihydrochloride
SS: Sodium Sulfite
AA: Ascorbic Acid
SFS: Rongalit (Sodium Formaldehyde Sulfoxylate)
Claims (1)
（Ｂ）一般式（Ｉ）で表される水酸基含有有機過酸化物；０．００５〜２質量部、
（Ｃ）還元剤；０．００５〜２質量部、および、
（Ｄ）水；１００〜１０００質量部、
を含むＮ−ビニルラクタム重合用組成物を水溶液重合に供することによって、Ｎ−ビニルラクタム重合体を得ることを特徴とする、Ｎ−ビニルラクタム重合体の製造方法。
(A) N-vinyllactam-containing vinyl monomer composition; 100 parts by mass,
(B) a hydroxyl group-containing organic peroxide represented by the general formula (I); 0.005 to 2 parts by mass,
(C) reducing agent; 0.005 to 2 parts by mass, and
(D) water; 100 to 1000 parts by mass,
A method for producing an N-vinyllactam polymer, characterized in that an N-vinyllactam polymer is obtained by subjecting an N-vinyllactam polymerization composition containing the above to aqueous solution polymerization .
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| JP3773408B2 (en) * | 2000-06-15 | 2006-05-10 | 第一工業製薬株式会社 | Method for producing vinylpyrrolidone polymer |
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| JP5946255B2 (en) * | 2010-09-17 | 2016-07-06 | 株式会社日本触媒 | N-vinyl lactam polymer and process for producing the same |
| JP6273855B2 (en) * | 2014-01-23 | 2018-02-07 | 日油株式会社 | Organic peroxide composition and method for polymerizing vinyl monomer using the same |
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